Chelsea Handler: Your Favorite Rapper's Favorite TV Personality

By Bridget Bland

There’s no television personality that has embraced hip-hop more than this year’s MTV Video Music Awards host, Chelsea Handler. The author and ‘Chelsea Lately’ late-night talk show host released a

statement shortly after her high-profile gig was announced, “This has been a huge year for hip-hop and rap, and it is well-known that I have the closest ties with these communities – musically and sexually."

She joked, "I am to rap and hippity-hop what Warren Buffet is to finance, minus the sex."

But, those who are fans of the 35 year-old comic can attest she really does support rappers - having them on her show to promote their albums, movies, books, and products over the years. After all, this is the same woman who sought advice on nailing a rapper from Erykah Badu.

Hit the jump to see our favorite Chelsea Handler rap connects and a flipbook of the talk show host with the MC's.


Handler has never denied her obsession with the King of the South. In between her compliments of his pretty smile and trying to get to the bottom of his romantic “situation,” Handler vowed to keep in touch when he went to prison. She loves him so much that she kept her word and sent him dirty magazines when he was serving his one year sentence. T.I.’s wife, Tiny, wasn’t too pleased and gave them all back when she appeared on ‘Lately’ to promote her show ‘Tiny and Toya.’ T.I. has since visited Handler and told the Atlanta rapper about her on-camera run-in with the mother of his children, joking, “She had never heard anything about our it was awkward.”

Fat Joe

Back in 2008, way before the likes of T.I., 50 Cent or Ludacris stopped by, Fat Joe became the first rapper to appear on ‘Chelsea Lately.’ She adores the Puerto Rican MC, telling him on his first

visit, “You’re very cute. I would like to snuggle with you.” When he returned she gave him his due, saying, “You broke my rapper cherry…and now I’m the town whore. “ She always asks when he's going to team with J.Lo again. The Bronx native also fondly told Handler “You’re a hell of a flirt, Chels,” foreshadowing her future with much of the hip-hop world.


The latest rapper to hit ‘Chelsea Lately,’ B.o.B. chatted up Handler about his five VMA nominations, opening for Eminem and Jay-Z and how he jump-started his career at 21 years old. The Grand Hustle artist shared that he’d yet to meet his ‘Airplanes’ collaborator, Paramore singer Haylee Williams. And, inevitabley Handler said “I know you are friends with my ex-lover, T.I.” She also said “That Tiny girl took him. I’m trying not to be angry about it. I’m just trying to move on with my life.” She asked him, “Have you spoken to him since she got locked up in jail again?” The crowd then went wild when Handler backed it up for B.o.B.


After his latest album ‘Battle of the Sexes’ topped the Billboard chart, Ludacris stopped by ‘Chelsea Lately’ to congratulate her on her New York Times Best-Seller. He brought along a bottle of his Conjure cognac emblazoned with naked pictures of Handler and they talked about riding around in his RV the next time she heads to Atlanta. Out of all of her rap guests, she seemed the most relaxed with Luda, focusing not on his bedroom behavior and instead inquiring about his city of Hotlanta for most of their interview.

Rick Ross, Big Boi, Lil’ Jon

Getting Rick Ross, Big Boi and Lil’ Jon to weigh in on current events cemented Handler as every rapper’s favorite late-night television stop. “You are not watching BET…this is our first-ever, all-rapper roundtable,” Handler said at the start of her show. The former Playboy cover girl shared that the idea was “a dream of mine ever since the inception of this show.” The guys filled Handler in on why black men love big butts and how they are able to handle things in the bedroom. Handler connected most with Rick Ross, who she told, “if I was gonna have sex with one of you, it would be you.”

50 Cent

As soon as these two got together trouble ensued. “You’re very, very cute, you know this,” the ‘Candy Shop’ MC told her. He probed,“Do you have a boyfriend? I deserve you. We’d be great.” The New Jersey native told 50, “You have the nice, sweet smile, like T.I.” 50 later tweeted that he thinks Handler is beautiful and she confirmed rumors that he tried to holler at her after appearing on the show, but at the time she was in a relationship and didn’t follow through on his offer.

Pharrell Williams

One of the first things that Chelsea and Pharrell spoke about during his visit to the show was how one of her staffers wanted him to be her sperm donor. Immediately, he inquired why she doesn’t want his sperm and their back and forth ensued. He admired her eyes and made nasty

jokes about Smurfs before sharing a story of how one of his friends is enamored with her ass. She let him cop a feel, like Akon did, at the close of the interview.

Chelsea Handler is sure to have more flirty interactions with rappers during her hosting duties this Sunday. The 27th annual MTV Video Music Awards will be broadcast live from the Nokia Theatre in Los Angeles on September 12. The party starts with MTV News' VMA Pre-Show at 8 p.m.,

followed by the main event at 9 p.m. ET.

Movie & TV Awards 2018